Our History

Chesapeake Roofing, Windows & Siding is a complete exterior remodeling company handling and roofing contractor siding, windows, roofing, sunrooms, doors, facia, and seamless gutters. The company is licensed, bonded and insured and a Better Business Bureau (BBB) of Greater Maryland Accredited Business.

Kurt Burkhart founded Chesapeake Roofing, Windows & Siding in 1987, after graduating from the University of Maryland. It quickly became a trusted name in the Anne Arundel county home improvement industry and local roofing contractors serving the greater Annapolis area.

Our specialty is the renovation of existing homes as opposed to new construction. This requires a great level of skill and customer service. It is a significant advantage that we offer all major exterior home improvement services, making Chesapeake Roofing, Windows & Siding a “one stop shop” for homeowners in and around Annapolis who are looking for a trusted roofing and home improvement contractor to help you meet your goals for improving home value or expanding your living space.

Chesapeake Roofing, Windows & Siding has specialized crews with more than 50 years of combined experience for each type of job. Our crews are certified as CertainTeed Master Shingle Applicators as well as Siding & Window Master Craftsmen.


Chesapeake Roofing,
Windows & Siding Inc.

910 Soaring Eagle Court,
Davidsonville, MD 21035

PO Box 4524
Crofton, MD 21114
MHIC #36354